Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to gamma-chiral alpha,beta-unsaturated acid derivatives

被引：28

作者：

Tomooka, K ^{[1
]}

Nagasawa, A ^{[1
]}

Wei, SY ^{[1
]}

Nakai, T ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT CHEM TECHNOL,MEGURO KU,TOKYO 152,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(96)02077-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The allylation of the dienolate derived from the chiral alpha, beta- or beta, gamma-unsaturated imide followed by the Cope rearrangement is shown to effect the net remote asymmetric induction to create anew chirality of either configuration at the gamma-position in high % de. The utility of this approach is shown in the asymmetric synthesis of the C6 side chain of zaragozic acid. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：8895 / 8898

页数：4

共 17 条

[1] Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary [J].